Making It with Jess Ekstrom

In this insightful episode of Making It with Jess Ekstrom, Jess sits down with Sabina Osorio, Senior Director of Growth Marketing for TED Conferences, to explore what transforms an idea into something people can understand, remember, and share.Sabina reveals the preparation behind a powerful TED Talk, including why speakers must edit ruthlessly, rehearse extensively, and resist the urge to sell from the stage. She also explains why TED receives thousands of submissions each week and what an idea needs to stand apart.Jess and Sabina also discuss the dark side of going viral, building genuine professional relationships without feeling transactional, and why being helpful is more valuable than chasing the largest possible audience. Sabina opens up about overcoming perfectionism, navigating imposter syndrome at TED, and redefining success as protecting her joy, family time, and life outside of work.EPISODE HIGHLIGHTSWhat Makes an Idea TED-Worthy: Sabina explains why a strong idea must be original, carefully researched, easy to understand, and relevant to people around the world.The Work Behind a TED Talk: Discover why speakers can spend more than 100 hours editing, fact-checking, rehearsing, and refining a single talk. Why Going Viral Shouldn’t Be the Goal: Sabina shares how viral content can attract the wrong audience and pull creators away from the community they actually want to serve. Stop Letting Perfectionism Hold You Back: Sabina reveals how she replaced the pursuit of perfection with an 80/20 mindset that allows her to act, learn, and grow.Build Relationships Before You Need Them: Learn how genuine curiosity, consistent connection, and offering value helped Sabina build the relationship that eventually opened the door to TED.Let Your Team Find Their Own Way: Sabina explains why leaders should resist stepping in too quickly and give capable people the space to solve problems differently.Redefining What It Means to Make It: Ten years ago, success meant climbing the corporate ladder. Today, Sabina measures it by joy, family time, hobbies, and a career that supports her life.

In this inspiring and eye-opening episode of Making It with Jess Ekstrom, Jess sits down in person with disability advocate, social entrepreneur, and author Tiffany Yu. Tiffany reflects on acquiring her disability at nine years old after a traumatic car accident that permanently paralyzed her arm. She opens up about the cultural shame, silence, and assimilation tactics she navigated for over a decade before eventually pivoting toward disability pride and community building. Tiffany breaks down the concept of the "assumption funnel" that systemically locks disabled people out of job markets and opportunities, while dismantling popular tropes like the "hero's journey" or "overcoming" disability. She also reveals how, at age 37, she began chasing joy by tapping into the interests of her nine-year-old self—a journey that ultimately led her to join the USA Paraclimbing Team with her eyes set on the LA 2028 Paralympics.Episode HighlightsThe "Assumption Funnel": Tiffany breaks down how societal assumptions—like assuming someone with a paralyzed arm cannot type or do an office job—create cascading barriers to employment, book deals, and basic accessibility.Moving Beyond Assimilation: How growing up in an immigrant household influenced Tiffany's early decisions to hide her disability and keep track of lies, and what finally sparked her journey toward disability pride.Dismantling the "Hero's Journey": Why narratives framing disabled people as "overcoming" their disabilities or accomplishing goals "in spite of" them are harmful, and why language should reflect living with disability.Handling Unsolicited Advice & Microaggressions: The mental fatigue of navigating intrusive questions, viral comment sections, and unsolicited medical advice, alongside the concept of trying to be a "sandbag clown".Reinventing Yourself at 37: How Tiffany re-engaged with hobbies her nine-year-old self loved, stepping onto a rock climbing wall 19 years after her accident despite internalizing doubts.Road to the LA '28 Paralympics: From tying for last at her first competition to earning a spot on the USA Paraclimbing Team and competing globally.Play, Fun, Joy (PFJ): Why rest and joy are valid forms of productivity, and how Tiffany balances her professional advocacy work with personal fulfillment.About Our GuestTiffany Yu is a disability advocate, social entrepreneur, speaker, and the author of The Anti-Ableist Manifesto. She is the founder of Diversability, an award-winning ecosystem democratizing visibility, community, and economic opportunity for disabled people. Named to the Forbes Accessibility 100 and a multi-time TED speaker, Tiffany is also a competitive athlete on the USA Paraclimbing Team working toward the LA 2028 Paralympic Games.

In this enlightening episode of Making It with Jess Ekstrom, Jess sits down with Claude Silver, the Chief Heart Officer at VaynerMedia and author of Be Yourself at Work. Claude opens up about her non-traditional path to executive leadership—from struggling with academics and feeling like a failure in her early 20s to finding her calling in transformative psychology and emotional intelligence. She pulls back the curtain on what a Chief Heart Officer actually does, how she helped shift VaynerMedia’s hiring philosophy from "culture fit" to "skillset fit and culture addition", and why feedback should be viewed as connection rather than correction. Plus, Claude shares her perspectives on parenting beyond grades, overcoming workplace gossip, and maintaining irreplaceable human connection in an era dominated by AI.Episode Highlights:Overcoming School Struggles: Claude reflects on how poor test scores affected her early confidence, realizing later in life that traditional schooling tests for the wrong skills while overlooking emotional intelligence.The "Kindness Balloon" & Parenting: How Claude teaches her children values like commitment, work ethic, and everyday kindness over simple academic performance.Ditching "Culture Fit": Why hiring for "culture fit" creates homogenous teams, and how VaynerMedia shifted to hiring for "skillset fit and culture addition" to foster real diversity of thought.What a Chief Heart Officer Does: Defining the role as serving as the emotional framework for a 2,000-person global company, balancing empathy and people-first culture with high-performance accountability.The Danger of Shrinking at Work: Addressing the cost of hiding your true self at work, and why "dipping your toe in the water" prevents burnout and mental health decline.Reframing Feedback as Connection: Why humans naturally fear feedback, and how managers can deliver specific, kind, current, and actionable feedback that builds trust.Analog Moments in an AI World: Why AI will handle data gathering and organizational efficiency, but human curiosity, raw vulnerability, and in-person (IRL) connection will remain the ultimate differentiator.Redefining "Making It": How Claude transitioned from working 15-hour weekend shifts to earn validation to prioritizing how she spends her time and choosing experiences that fill her spiritual and relational bucket.About Our Guest:Claude Silver is the Chief Heart Officer at VaynerMedia, where she serves as the emotional framework for over 2,000 employees globally. A former advertising executive with a background in transformative psychology, Claude is a renowned speaker and the author of Be Yourself at Work. Her mission centers on scaling empathy, emotional intelligence, and relational connection within fast-paced corporate environments, empowering individuals to unlock their full potential and bring their authentic selves to work every day.

In this energizing episode of Making It with Jess Ekstrom, Jess sits down with Claire Coder, the visionary founder of Aunt Flow. Claire shares the exact moment at age 18 that inspired her to drop out of college to make tampons and pads just as free, dignified, and accessible as toilet paper in public restrooms. She opens up about the evolution of her company—from packing subscription boxes in a U-Haul storage unit to raising nearly $17 million in venture capital and stocking Aunt Flow dispensers across 70,000 bathrooms worldwide. Claire provides a candid look at the realities of being a B2B founder, including why she considers entrepreneurship a "genetic defect," navigating the surprising pushback she gets from female decision-makers, and why balancing a world-changing social impact requires owning a unapologetically capitalist mindset.Episode Highlights:The "Quarter Dispenser" Moment: Claire recalls her monumental 18th-period story that exposed the lack of basic period care in public restrooms and sparked the idea for Aunt Flow.Dropping Out for Menstruation: Navigating the awkward, bold conversations with parents and advisors when leaving Ohio State University after one semester to build a period care empire.From U-Haul to B2B Leader: The scrappy early days of running a subscription box out of a 3rd-floor apartment and storage unit before pivoting to patented B2B bathroom dispensers.A Shift in Policy: Celebrating the legal and cultural shift across 27 states that now mandate or fund free period products in school bathrooms."No Mission Without Margin": A raw masterclass on why purpose-driven startups must maintain for-profit discipline and high performance to create true long-term impact.Selling Tampons to Men vs. Women: Why heads of facilities (mostly men) are often an easy sell, and the unexpected challenge of overcoming internalized taboo from female decision-makers.Handling 86 VCs Rejections: What Claire learned while pitching investors, raising $17M, and how she gives direct, constructive feedback to the next generation of founders.The Art of "Playing the Game": Why context-switching and matching the energy of any room—from janitorial trade shows to Manhattan rooftops—is a essential founder superpower.About Our Guest:Claire Coder is the founder and CEO of Aunt Flow, a B2B company that designs and installs patented, free-play dispensers packed with organic cotton tampons and pads in public and corporate bathrooms. After dropping out of college at age 18 to solve period poverty and bathroom inequality, Claire has built Aunt Flow into a global brand operating in over 70,000 bathrooms across all 50 states and multiple countries. She has raised nearly $17 million in venture capital, donated over 7 million period products to communities in need, and continues to champion menstrual equity worldwide.

Jess sits down with Libby Ward, the creator behind the viral movement Diary of an Honest Mom and author of Honest Motherhood. Libby shares her personal evolution from a self-described people-pleasing "plate spinner" to a fierce advocate for maternal mental health. She opens up about the crushing shift from the "baby parade" celebration of pregnancy to the overwhelming isolation of postpartum depression and medical emergencies. Libby also details her decision to step back from teaching, how viral TikTok success changed her relationship with content creation, her choice to keep her children's faces off social media, and how she unlearned decade-long habits of self-doubt to proudly own the value of her work and story.Episode Highlights:The "Baby Parade" Trap: Libby unpacks how society showers pregnant women with celebration, only to leave mothers feeling invisible once the baby arrives.The Postpartum Reality Check: A raw reflection on navigating a newborn medical emergency and mastitis in a hospital recliner, realizing how quickly a mother's basic needs are sidelined.Sociology & "Cycle Breaking": How returning to university in her 30s introduced Libby to terms like mental load and patriarchy, revealing that her burnout was systemic rather than a personal failure.Finding Community on TikTok: The origin of Diary of an Honest Mom and how going viral provided a safe testing ground to dismantle maternal shame.Protecting Kids in the Digital Age: Why Libby strictly keeps her children off camera, respecting their autonomy and avoiding the pressure of converting family life into content.Overcoming the Fear of "Selling": How years of therapy helped Libby transition from endlessly giving free content to confidently owning the life-changing value of her book.Redefining "Making It": Why success today isn't about the next book launch or viral video, but the rare, grounded ability to be fully present in the moment right in front of her.About Our Guest:Libby Ward is a digital creator, speaker, maternal mental health advocate, and the author of Honest Motherhood. Known digitally as Diary of an Honest Mom, Libby launched her platform to break cycles of shame, martyrdom, and perfectionism in parenting. With millions of followers across social platforms, she provides a refreshing, unfiltered look at mental health, division of labor, and the realities of modern motherhood, empowering women to prioritize their well-being and own their inherent worth.